JPH0229411A - Novel production of petroleum resin suitable for production of printing ink, varnish and paint - Google Patents
Novel production of petroleum resin suitable for production of printing ink, varnish and paintInfo
- Publication number
- JPH0229411A JPH0229411A JP1140957A JP14095789A JPH0229411A JP H0229411 A JPH0229411 A JP H0229411A JP 1140957 A JP1140957 A JP 1140957A JP 14095789 A JP14095789 A JP 14095789A JP H0229411 A JPH0229411 A JP H0229411A
- Authority
- JP
- Japan
- Prior art keywords
- fraction
- aromatic
- resin
- dicyclopentadiene
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011347 resin Substances 0.000 title claims abstract description 32
- 229920005989 resin Polymers 0.000 title claims abstract description 32
- 239000003208 petroleum Substances 0.000 title claims description 16
- 239000000976 ink Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000002966 varnish Substances 0.000 title claims description 9
- 239000003973 paint Substances 0.000 title claims description 8
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 239000002841 Lewis acid Substances 0.000 claims abstract description 6
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 6
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 5
- 239000003849 aromatic solvent Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 9
- 238000012719 thermal polymerization Methods 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 abstract description 6
- 150000001768 cations Chemical class 0.000 abstract description 2
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 4
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical compound C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- QROGIFZRVHSFLM-UHFFFAOYSA-N trans-beta-methyl styrene Natural products CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 3
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 2
- KXYDGGNWZUHESZ-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3h-chromen-4-yl)phenol Chemical compound C12=CC=CC=C2OC(C)(C)CC1(C)C1=CC=C(O)C=C1 KXYDGGNWZUHESZ-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- QROGIFZRVHSFLM-KXFIGUGUSA-N [(z)-prop-1-enyl]benzene Chemical compound C\C=C/C1=CC=CC=C1 QROGIFZRVHSFLM-KXFIGUGUSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 cyclic diolefins Chemical class 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- SQMZNUYQLISRTD-UHFFFAOYSA-N 4-propan-2-ylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(C(C)C)C2 SQMZNUYQLISRTD-UHFFFAOYSA-N 0.000 description 1
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/108—Hydrocarbon resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Polyethers (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、印刷インキ、ワニスおよび塗料の製造に適し
た石油樹脂の新規な製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a new process for the production of petroleum resins suitable for the production of printing inks, varnishes and paints.
従来の技術
ある種の用途、特に、印刷インキ、ワニスおよび塗料の
分野では、軟化点が高く、しかも、希釈性に優れ、且つ
溶剤、特に脂肪族系の溶剤に良く溶ける石油樹脂が必要
である。現在知られている石油樹脂は、溶剤、特に、脂
肪族系溶剤への希釈性と可溶性が極めて低いため、印刷
インキおよびワニスの製造用に使用することはほとんど
できない。Prior Art Certain applications, particularly in the field of printing inks, varnishes and paints, require petroleum resins with a high softening point, good dilutability and good solubility in solvents, especially aliphatic solvents. . Currently known petroleum resins can hardly be used for the production of printing inks and varnishes because of their very low dilutability and solubility in solvents, especially aliphatic solvents.
発明が解決しようとする課題
本発明の目的は、印刷インキ、ワニスおよび塗料の製造
に適した芳香族石油樹脂の製造方法を提供することにあ
る。Problems to be Solved by the Invention An object of the present invention is to provide a method for producing an aromatic petroleum resin suitable for producing printing inks, varnishes, and paints.
課題を解決するための手段
本発明の提供する印刷インキ、ワニスおよび塗料の製造
に適した芳香族石油樹脂の製造方法は、０６〜Ｃ３２の
芳香族留分によって構成される生成物と、ジシクロペン
タジェン留分の熱重合によって得られる樹脂とを、これ
ら２つの重重比ニ
ジシクロペンクジエン樹脂
芳香族留分
が０から１００となる範囲、特に、Ｏから５０となる範
囲で使用して、カチオン共重合することによって製造し
、しかも、これらを共重合する前にジシクロペンタジェ
ンの熱重合によって得られる上記樹脂を上記Ｃ６〜Ｃ１
゜の芳香族留分に溶解させることを特徴としている。Means for Solving the Problems The present invention provides a method for producing an aromatic petroleum resin suitable for producing printing inks, varnishes, and paints. The resin obtained by thermal polymerization of the pentadiene fraction is used in a range where the weight ratio of the two dicyclopenc diene resin aromatic fractions is from 0 to 100, particularly from O to 50, to form a cation. The above resin is produced by copolymerization, and before copolymerizing, the above resin obtained by thermal polymerization of dicyclopentadiene is added to the above C6 to C1.
It is characterized by being dissolved in the aromatic fraction of °.
本発明の方法によって得られる芳香族石油樹脂は高い軟
化点を有し、しかも、溶剤、特に脂肪族系溶剤への希釈
性と可溶性に優れているので、印刷インキ、塗料および
ワニスの製造に使用することができる。The aromatic petroleum resin obtained by the method of the present invention has a high softening point and has excellent dilutability and solubility in solvents, especially aliphatic solvents, so it can be used in the production of printing inks, paints, and varnishes. can do.
本発明の方法によって製造される樹脂は、上記２種類の
化合物をカチオン共重合させることによって得られる。The resin produced by the method of the present invention is obtained by cationic copolymerization of the above two types of compounds.
第１の化合物は、ジシクロペンタジェン留分を熱重合さ
せることによって得られる。このジシクロペンタジェン
留分の熱重合は、例えば、ジシクロペンタジェン留分と
芳香族系溶媒とを５０１５０の重量比にした混合物を２
から１０時間、２４０〜２７０℃の温度に維持すること
によって連続的に実施される。ジシクロペンタジェン留
分は石油留分を水蒸気でクラッキング（分解）すること
によって得られ、通常は下記の組成（重量％）を有して
いる
ジシクロペンタジェン ニア０〜９５ジシクロ
ペンタジエンコダイマー： １〜６メチルジシクロペン
タジエン 二０．２〜１０トリメチルジシクロペンタ
ジェン： ０．００５〜２５−ビニルノルボルネン
： １〜２イソプロピルノルボルネン ：
１〜１２（同定できない軽質分）＝３０未満
本発明の方法で使用する第２の化合物はＣ６〜Ｃ１２の
芳香族留分によって構成されている。The first compound is obtained by thermally polymerizing a dicyclopentadiene fraction. Thermal polymerization of this dicyclopentadiene fraction can be carried out, for example, by preparing a mixture of the dicyclopentadiene fraction and an aromatic solvent at a weight ratio of 50,150.
It is carried out continuously by maintaining the temperature from 240 to 270° C. for 10 hours. Dicyclopentadiene fraction is obtained by cracking (decomposition) of petroleum fraction with steam, and usually has the following composition (wt%): dicyclopentadiene codimer 0-95 dicyclopentadiene codimer : 1-6 methyldicyclopentadiene 20.2-10 trimethyldicyclopentadiene: 0.005-25-vinylnorbornene
: 1-2 isopropylnorbornene :
1-12 (unidentifiable light fraction) = less than 30 The second compound used in the method of the invention is constituted by a C6-C12 aromatic fraction.
このＣ６〜Ｃ１゜の芳香族留分は、大抵の場合、ナフサ
、ケロシンおよびガスオイルを含む石油原料の水蒸気分
解によって得られるが、−船釣には通常使用されている
任意の石油原料を水蒸気分解して得ることができる。こ
れらの石油原料の沸点は、一般に、２０〜２４５℃であ
り、これを分別蒸留することによって０８〜ＣＩ２の芳
香族留分と環状ジオレフィンを含む留分とが回収される
。この０６〜ＣＩ２留分の組成は一定ではなく、用いた
石油原料の種類によって決まる。This C6-C1° aromatic fraction is most often obtained by steam cracking of petroleum feedstocks including naphtha, kerosene and gas oil, but - any petroleum feedstock commonly used in boat fishing can be steam cracked. It can be obtained by disassembling it. The boiling point of these petroleum raw materials is generally 20 to 245°C, and by fractionally distilling them, aromatic fractions of 08 to CI2 and a fraction containing cyclic diolefins are recovered. The composition of this 06-CI2 fraction is not constant and is determined by the type of petroleum raw material used.
このＣ６〜ＣＩ。の芳香族留分は重合可能で、般には、
下記の組成（重量％）を有している：スチレン
：０．５〜１４アリルベンゼン
：０．５〜２α−メチルスチレン
： １〜８シスーβ−メチルスチレン ：０．２〜
１トランス−β−メチルスチレン ； １〜６ビニルト
ルエン ニア 〜２２インデン
： ５〜２１メチルインデン＋ジビニ
ルベンゼン：０．２〜９ジシクロペンクジエン
：０．４〜１２本発明の方法は、上記定義の２種類の
化合物または生成物をカチオン共重合することによって
実施されるが、ジシクロペンタジェン留分の重合によっ
て得られた生成物すなわち樹脂は、Ｃ６〜Ｃ１２の芳香
族留分に予め希釈しておく。This C6~CI. The aromatic fraction of is polymerizable and generally
It has the following composition (wt%): Styrene
:0.5-14 allylbenzene
:0.5-2α-methylstyrene
: 1-8 cis-β-methylstyrene: 0.2-
1 trans-β-methylstyrene; 1-6 vinyltoluene ~22 indene
: 5-21 methyl indene + divinylbenzene: 0.2-9 dicyclopenc diene
:0.4-12 The method of the present invention is carried out by cationic copolymerization of two types of compounds or products as defined above, but the product obtained by polymerization of the dicyclopentadiene fraction, i.e., the resin is diluted in advance with a C6 to C12 aromatic fraction.
カチオン重合は、５０℃以下の温度でルイス酸の存在化
で、公知の方法で実施される。このルイス酸は、用いた
上記２つの生成物に対して０．０２〜３重１％の割合で
使用される。ルイス酸としては、三弗化硼素とその錯体
が挙げられる。Cationic polymerization is carried out in the presence of a Lewis acid at a temperature below 50° C. in a known manner. This Lewis acid is used in a proportion of 0.02 to 1% by weight based on the above two products used. Lewis acids include boron trifluoride and its complexes.
本発明の方法では、本発明方法を実施するために使用さ
れる上記２種類の生成物を任意の比率で用いることがで
きる。すなわち、
ジシクロペンタジェン樹脂
芳香族留分
の重量比をＯ〜１００の範囲にして実施することができ
るが、特に、０〜５０の範囲が好ましい。In the process of the invention, any ratio of the two products mentioned above used for carrying out the process of the invention can be used. That is, the weight ratio of the aromatic fraction of the dicyclopentadiene resin can be set in a range of 0 to 100, but a range of 0 to 50 is particularly preferable.
本発明方法によって得られる石油樹脂は、広い分野に応
用することができる。特に、軟化点が１２０℃以上と高
く、しかも、溶剤、特に脂肪族系溶剤への希釈性と可溶
性が優れているので、本発明方法によって得られる石油
樹脂は、ワニス、塗料および印刷インキの製造に適して
いる。The petroleum resin obtained by the method of the present invention can be applied to a wide range of fields. In particular, the petroleum resin obtained by the method of the present invention has a high softening point of 120°C or higher, and has excellent dilutability and solubility in solvents, especially aliphatic solvents. suitable for
この場合、これらの用途では、例えば、脂肪族系溶剤混
合物６０〜４０重量％に対して上記石油樹脂が４０〜６
０重量％の割合で添加される。In this case, in these applications, for example, the amount of the petroleum resin is 40 to 6% by weight based on 60 to 40% by weight of the aliphatic solvent mixture.
It is added in a proportion of 0% by weight.
本発明は、下記の実施例によってより明らかとなろう。The invention will become clearer from the following examples.
実施例中の量は、全て、重量部で示されている。All amounts in the examples are given in parts by weight.
実施例１：
熱重合
（ａ）′熱重合によるジシクロペンタジェン樹脂の製造
加熱したオイルを循環させることによって加熱可能なジ
ャケットと、冷水を循環させることによって冷却可能な
ステンレス鋼製の内部コイルと、「アンカー（Ａｎｃｈ
ｏｒ） Ｊ型撹拌器とを備えたステンレス鋼製のグリニ
ヤール（Ｇｒｉｇｎａｒｄ）型オートクレーブに下記組
５！２（重量％）・スチレン
２．８９α−メチルスチレン １．７
９β−メチルスチレン ０．６８トラン
ス−β−メチルスチレン ２．２５ビニルトルエン
２２．旧インデン
１２．９３メチルインデン＋ジビニルベン
ゼン ３．３７ジシクロペンタジエン
０．６１のＣ６〜ＣＩ２の芳香族留分８重１部を導入す
る。Example 1: Thermal Polymerization (a)' Preparation of Dicyclopentadiene Resin by Thermal Polymerization A jacket that can be heated by circulating heated oil and an inner coil made of stainless steel that can be cooled by circulating cold water. , "Anchor"
or) In a stainless steel Grignard type autoclave equipped with a J type stirrer, the following set 5!2 (wt%) styrene was added.
2.89α-methylstyrene 1.7
9 β-methylstyrene 0.68 trans-β-methylstyrene 2.25 vinyltoluene 22. old inden
12.93 Methylindene + Divinylbenzene 3.37 Dicyclopentadiene
1 part of 0.61 C6-CI2 aromatic fraction 8 parts is introduced.
次に、下記の組成（重量％）ニ
ジシクロペンタジェン ７５．３６メチル
ジシクロペンタジエン ０．２８トリメチルジシ
クロペンタジエン ０．０５ジシクロペンタジエンコ
ダイマ−３，４３イソプロピルノルボルネン
１１．０８５−ビニルノルボルネン １．
１２軽質成分 ０．８４同定
できないもの ３．６４のジシクロペ
ンタジェン７１重量部を反応装置に添加する。Next, the following composition (wt%) Nidicyclopentadiene 75.36 Methyldicyclopentadiene 0.28 Trimethyldicyclopentadiene 0.05 Dicyclopentadiene codimer-3,43 Isopropyl norbornene
11.085-vinylnorbornene 1.
12 Light components 0.84 Unidentified 3.64 71 parts by weight of dicyclopentadiene are added to the reactor.
さらに、キシレン２１重１部を添加する。この反応混合
物を２７０℃で８時間加熱する。反応装置内の圧力は９
バールに達する。Furthermore, 1 part by weight of xylene 21 is added. The reaction mixture is heated at 270° C. for 8 hours. The pressure inside the reactor is 9
Reach the crowbar.
樹脂溶液を回収する。反応収率は、使用した供給原料を
基準で６４．７％であり、反応物の転化率は９３％であ
る。Collect the resin solution. The reaction yield is 64.7% based on the feedstock used and the conversion of reactants is 93%.
得られた樹脂のボール軟化点は１５５℃（ＡＳＴＭ
Ｅ２８規格によって測定）であり、この樹脂とイソドデ
カンとの混合物（５０１５０）で測定した曇り点は６０
℃である。The ball softening point of the obtained resin was 155°C (ASTM
E28 standard) and the cloud point measured for a mixture of this resin and isododecane (50150) is 60
It is ℃.
ら）本発明による樹脂の製造
ジシクロペンタジェン留分から上記のように製造された
樹脂を０６〜ＣＩ□の芳香族留分中に希釈する。) Preparation of the resin according to the invention The resin prepared as described above from the dicyclopentadiene fraction is diluted in an aromatic fraction of 06 to CI□.
このＣ６〜ＣＩ２の芳香族留分の組成は以下の通りであ
る：
スチレン ４．７８α−メチルス
チレン １．７７シス−β−メチルスチレン
２．４０トランス−β−メチルスチレン ２．５
４ビニルトルエン １５．７４インデン
１００６メチルインデン
７．６２上記２つの生成物（樹脂と０６〜
ＣＩ２の芳香族留分）の相対量を変えて重合した。この
重合は、ルイス酸としての三弗化硼素の存在下で実施さ
れる。使用した反応物の量と、操作条件と、得られた最
終製品である樹脂の特性は第１表にまとめて示しである
。The composition of this C6-CI2 aromatic fraction is as follows: Styrene 4.78 α-methylstyrene 1.77 cis-β-methylstyrene 2.40 trans-β-methylstyrene 2.5
4 vinyl toluene 15.74 indene 1006 methyl indene
7.62 The above two products (resin and 06~
Polymerizations were carried out with varying relative amounts of the aromatic fraction of CI2. This polymerization is carried out in the presence of boron trifluoride as Lewis acid. The amounts of reactants used, the operating conditions, and the properties of the final resin obtained are summarized in Table 1.
実施例２
実施例１を繰り返した。ただし、Ｃ６〜ＣＩ２の芳香族
留分としては下記組成のものを使用した：
スチレン １０．１７α−）、１
ｅ スチレン ２．１１シス−β−Ｍｅ
スチレン ４．２２トランス−β−・：Ａｅ
スチレン ３．９１ビニルトルエン
１１．１９インデン ２０．
８６Ｍｅ スチレン ３．２１操作
条件と得られた結果は下記第２表に示しである。Example 2 Example 1 was repeated. However, the aromatic fraction of C6 to CI2 used had the following composition: Styrene 10.17α-), 1
e Styrene 2.11cis-β-Me
Styrene 4.22 trans-β-・:Ae
Styrene 3.91 vinyl toluene
11.19 Inden 20.
86Me Styrene 3.21 The operating conditions and results obtained are shown in Table 2 below.
第２表Table 2
Claims (5)
れる生成物と、ジシクロペンタジエン留分の熱重合によ
って得られる樹脂とを、これら２つの重量比： ジシクロペンタジエン樹脂／芳香族留分 が０から１００となる範囲で使用して、カチオン共重合
し、しかも、これら２つを共重合する前にジシクロペン
タジエンの熱重合によって得られる上記樹脂を上記Ｃ＿
６〜Ｃ＿１＿２の芳香族留分に溶解させることを特徴と
する印刷インキ、ワニスおよび塗料の製造に適した芳香
族石油樹脂の製造方法。(1) A product composed of aromatic fractions C_6 to C_1_2 and a resin obtained by thermal polymerization of a dicyclopentadiene fraction are mixed in a weight ratio of these two: dicyclopentadiene resin/aromatic fraction. C_
A method for producing an aromatic petroleum resin suitable for producing printing inks, varnishes, and paints, characterized by dissolving it in an aromatic fraction of 6 to C_1_2.
あることを特徴とする請求項１に記載の方法。2. A method according to claim 1, characterized in that the weight ratio of said product to said resin is from 0 to 50.
℃以下の温度で実施されることを特徴とする請求項１ま
たは２に記載の方法。(3) When the above cationic copolymerization is performed in the presence of a Lewis acid,
3. A method according to claim 1 or 2, characterized in that it is carried out at a temperature below .degree.
族溶剤の存在下で、この混合物を２４０〜２７０℃の温
度に２〜１０時間維持して実施されることを特徴とする
請求項１から３のいずれか１項に記載の方法。(4) Thermal polymerization of the dicyclopentadiene fraction is carried out in the presence of an aromatic solvent by maintaining the mixture at a temperature of 240 to 270°C for 2 to 10 hours. 3. The method according to any one of 3.
って得られた樹脂を用いた印刷インキ、ワニスおよび塗
料。(5) Printing inks, varnishes, and paints using the resin obtained by the method according to any one of claims 1 to 4.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8807420 | 1988-06-03 | ||
| FR8807420A FR2632311B1 (en) | 1988-06-03 | 1988-06-03 | NOVEL PROCESS FOR THE MANUFACTURE OF OIL RESINS SUITABLE FOR THE MANUFACTURE OF PRINTER INKS, VARNISHES AND PAINTS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0229411A true JPH0229411A (en) | 1990-01-31 |
Family
ID=9366922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1140957A Pending JPH0229411A (en) | 1988-06-03 | 1989-06-02 | Novel production of petroleum resin suitable for production of printing ink, varnish and paint |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4983682A (en) |
| EP (1) | EP0345124A1 (en) |
| JP (1) | JPH0229411A (en) |
| KR (1) | KR900000396A (en) |
| BR (1) | BR8902540A (en) |
| FR (1) | FR2632311B1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04200831A (en) * | 1990-10-24 | 1992-07-21 | Shimpo Ind Co Ltd | Device for bundling reinforcing steels |
| JPH06170476A (en) * | 1991-04-23 | 1994-06-21 | Nikko Co Ltd | Reinforcement binding device |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5171793A (en) * | 1990-02-22 | 1992-12-15 | Exxon Chemical Patents Inc. | Hydrogenated resins, adhesive formulations and process for production of resins |
| US5391670A (en) * | 1993-08-09 | 1995-02-21 | Hercules Incorporated | Alkylation resins from polycyclic aromatic compounds |
| EP0802251B1 (en) * | 1996-04-15 | 2003-10-15 | Eastman Chemical Resins, Inc. | Styrenic block copolymer based hot-melt adhesives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1486211A (en) * | 1974-03-04 | 1977-09-21 | Exxon Research Engineering Co | Petroleum resins |
| JPS5580415A (en) * | 1978-12-13 | 1980-06-17 | Toyo Soda Mfg Co Ltd | Preparation of petroleum resin |
| US4558107A (en) * | 1982-06-11 | 1985-12-10 | Exxon Research & Engineering Co. | Aromatic high softening point petroleum resins and process for its preparation |
| JPS60139709A (en) * | 1983-12-27 | 1985-07-24 | Nippon Zeon Co Ltd | Production of cyclopentadiene polymer |
| JPS60228515A (en) * | 1984-04-26 | 1985-11-13 | Nippon Zeon Co Ltd | Production of graft polymer |
-
1988
- 1988-06-03 FR FR8807420A patent/FR2632311B1/en not_active Expired - Fee Related
-
1989
- 1989-05-25 EP EP89401429A patent/EP0345124A1/en not_active Withdrawn
- 1989-06-02 BR BR898902540A patent/BR8902540A/en not_active Application Discontinuation
- 1989-06-02 KR KR1019890007623A patent/KR900000396A/en not_active Application Discontinuation
- 1989-06-02 JP JP1140957A patent/JPH0229411A/en active Pending
- 1989-06-05 US US07/361,069 patent/US4983682A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04200831A (en) * | 1990-10-24 | 1992-07-21 | Shimpo Ind Co Ltd | Device for bundling reinforcing steels |
| JPH06170476A (en) * | 1991-04-23 | 1994-06-21 | Nikko Co Ltd | Reinforcement binding device |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0345124A1 (en) | 1989-12-06 |
| FR2632311A1 (en) | 1989-12-08 |
| KR900000396A (en) | 1990-01-30 |
| BR8902540A (en) | 1990-03-20 |
| US4983682A (en) | 1991-01-08 |
| FR2632311B1 (en) | 1990-08-17 |
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